(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carboxylic acid

• ChemBase ID: 166717
• Molecular Formular: C21H27FO5
• Molecular Mass: 378.4344832
• Monoisotopic Mass: 378.18425218
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)O)C)C)O)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)O)C)C)C
• InChI: InChI=1S/C21H27FO5/c1-11-8-15-14-5-4-12-9-13(23)6-7-18(12,2)20(14,22)16(24)10-19(15,3)21(11,27)17(25)26/h6-7,9,11,14-16,24,27H,4-5,8,10H2,1-3H3,(H,25,26)/t11-,14+,15+,16+,18+,19+,20+,21+/m1/s1
• InChIKey: PFAGPIFFRLDBRN-AFKBWYBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• IUPAC Traditional name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• Synonyms: (11β,16α,17α)-9-Fluoro-11,17-dihydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carboxylic Acid; 9-Fluoro-11β,17-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic Acid; (-)-Dexamethasone Acid

Database IDs

• CAS Number: 37927-01-8
• PubChem SID: 162260850
• PubChem CID: 12878399

CALCULATED PROPERTIES

• Acid pKa: 4.2738895
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.92017037
• LogD (pH = 7.4): -0.8126566
• Log P: 2.1691923
• Molar Refractivity: 97.2396 cm^3
• Polarizability: 37.61653 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >263°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D298805

A glucocorticoid receptor of spleen tumor of human, a steroid for inhibiting angiogenesis and tumor growth and treating ocular hypertension.

REFERENCES

• Manz, B., et al.: J. Steroid Biochem., 17, 335 (1982)
• Manz, B., et al.: J. Clin. Chem. Clin. Biochem., 22, 209 (1984)